Rongalite as a Methylene Surrogate: Synthesis of Heterodiarylmethanes <i>via</i> C(sp<sup>2</sup>)-H Functionalization
Sanjeeva Thunga, Madhu Inapanuri, Neetika Singh, Hari Prasad Kokatla
Abstract
An efficient method for the synthesis of heterodiarylmethanes through the coupling of imidazo[1,2- a ]pyridines and heteroarenes using indoles employing rongalite as a methylenating reagent has been developed. This regioselective C–H functionalization provides a wide range of heterodiarylmethanes of imidazo[1,2- a ]pyridines and imidazo[2,1- b ]thiazole. Here, rongalite plays a crucial role in generating a C1 unit in situ, which triggers the heterodiarylmethylation process. The use of inexpensive rongalite (ca. $0.03/1 g), mild reaction conditions, and gram-scale synthesis are some of the key features of this methodology.
Topics & Concepts
Surface modificationReagentRegioselectivityThiazoleChemistryCombinatorial chemistryMethyleneStereochemistryMedicinal chemistryOrganic chemistryCatalysisPhysical chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions